Leonard Osterman, better known by the nickname Crow, is Ben Caspere's murderer. He is later revealed to be the vengeful son of a married couple, who were robbed of diamonds and killed by corrupt Vinci police officers during the 1992 L.A. riots. He appears as one of the two main antagonists in the second season of True Detective.

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Crow killed Ben Caspere by dissolving his eyes with hydrochloric acid and then shooting him in the groin with a shotgun point blank, resulting in what the coroner described as a trauma induced heart attack. Caspere's body was then bound and left vertical.

Unconscious, Ray envisions himself at a bar, watching a Conway Twitty impersonator perform Bette Midler's 'The Rose'. His father sits across from him in full police regalia; he cryptically narrates the circumstances of Ray's supposed death, after which Ray sees fatal wounds appear on his person.

Waking up with broken ribs and urine-soaked pants, Ray realizes the bullets were non-lethal riot shells. Police converge on the house, and Ray shares dialogue with Bezzerides before being taken away to be treated for his injuries. Later Ray meets with Frank and demands explanation who else knew about Ben's second house and wants to know what's the real connection between Frank and Ben before he get's shot by the real bullets.

Velcoro and Bezzerides learn of Paul's death and resolve to close the case. They identify Laura, Caspere's secretary, and Lenny, a photographer from the movie set of the stolen prop car, as the Osterman siblings. Visitng Lenny's home they find Laura handcuffed to the fireplace. She reveals that Lenny murdered Caspere, and plans to kill William Holloway under the pretense of a public meeting at a train station to trade Caspere's tapes for money. Bezzerides puts Laura on a bus to Seattle while Velcoro intercepts Lenny at the train station and convinces him to entrap Holloway. Velcoro takes Lenny's place, leading Holloway into a discussion about the blue diamond conspiracy with him while Lenny sits nearby, wearing a wire. However, when Holloway reveals that Caspere actually fathered Laura while doing business with her mother, Lenny is consumed by pure rage and stabs Holloway, they begin to struggle for the knife as a shootout starts between Burris, Velcoro and Bezzerides. Velcoro, Bezzerides and Burris escape while Lenny and Holloway are shot to death by law enforcement agents and his tape of the conversation is unintentionally destroyed in the commotion, thus preventing Velcoro's and Bezzerides' original plan to incriminate Holloway and the entire Vinci PD.

After escaping to Venezuela with Jordan and Nails, Ani gives birth to Ray's second child and before the four disappear, they pass to a journalist crucial and incriminating evidence which exposes Caspere, Burris, Dixon and Holloway as the perpetrators of the robbery-murder in 1992, exposes the corruption which plagues Vinci and also likely exposes Lenny Osterman as the man behind Caspere's murder.

Lenny appeared to be an acutely insane, vengeful, impulsive, cunning, psychopathic and sadistic serial killer, whose only determination was to track down and kill in a very gruesome and merciless way the individuals, who were responsible for the deaths of his parents. He also appeared to be very hot-tempered as seen by his violent reaction when he heard that Caspere was the true father of his sister Laura and immediately jumped on Holloway with a knife. Even though Holloway managed to shoot Lenny once in the stomach, Lenny barely flinched at his wound as he was blinded by pure rage and managed to fatally stab Holloway before law enforcement agents gun down Lenny for good.

His weapon of choice is a standard 12 gauge shotgun, which he uses with the tendency to shoot the genitals of his victim. Crow's signature is his victim being left with HCl acid-poured eyes. He also appeared to carry a knife as a back-up weapon which he most notably used when he killed Chief Holloway.